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WO2013165476A1 - Feeding deterrence in agricultural pests such as hemiptera, lepidoptera and coleoptera - Google Patents

Feeding deterrence in agricultural pests such as hemiptera, lepidoptera and coleoptera Download PDF

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Publication number
WO2013165476A1
WO2013165476A1 PCT/US2013/000120 US2013000120W WO2013165476A1 WO 2013165476 A1 WO2013165476 A1 WO 2013165476A1 US 2013000120 W US2013000120 W US 2013000120W WO 2013165476 A1 WO2013165476 A1 WO 2013165476A1
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carbon atoms
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compound
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compounds
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French (fr)
Inventor
Robert H. Bedoukian
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Bedoukian Research Inc
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Bedoukian Research Inc
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Priority to CN201380022820.4A priority Critical patent/CN104334021B/en
Priority to US14/390,826 priority patent/US10111429B2/en
Priority to JP2015510248A priority patent/JP6133404B2/en
Priority to EP13784833.9A priority patent/EP2925126A4/en
Publication of WO2013165476A1 publication Critical patent/WO2013165476A1/en
Anticipated expiration legal-status Critical
Priority to US16/131,412 priority patent/US20190082690A1/en
Priority to US16/531,446 priority patent/US11224223B2/en
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof

Definitions

  • This invention relates to the use of compounds as agents that deter feeding of crops by agricultural pests such as hemiptera, lepidoptera and coleoptera including, but not limited to, stink bugs, codling moth larvae and granary weevils.
  • the active feeding deterrence agents of this invention are an effective control agent against agricultural pests such as hemiptera, lepidoptera and coleoptera.
  • Hemiptera includes cicadas, aphids and stink bugs such as the Brown Marmorated Stink Bug.
  • Lepidoptera includes butterflies and moths such as the Codling Moth.
  • Coleoptera are beetles and the order contains granary weevils.
  • Agricultural pests including but not limited to the brown marmorated stink bug, codling moth and granary weevil are known to feed on various crops causing damage to fruits, vegetables and other plant life. The cost of this damage is extensive and leads to hardship among growers.
  • Codling moth larvae penetrate into apples and pears and tunnel to the core, leaving holes in the fruit that are filled with reddish-brown, crumbly droppings. If left uncontrolled, larvae can cause substantial damage, often infesting 20 to 90% of the fruit, depending on the variety and location. Late maturing varieties are more likely to suffer severe damage than early varieties. [J. L. Caprile and P.M. Vossen, Pest Notes: Codling Moth UC ANR Publication 7412, May 2011].
  • Phosmet a phthalimide-derived, non-systemic, organophosphate insecticide is the primary means of controlling codling moth damage to apples. This material is on the US Emergency Planning list of extremely hazardous substances and is highly toxic to bees. The materials covered in this patent application would be a much gentler means of deterring the larvae and controlling moth infestation.
  • Granary weevils are attracted to and will attack all kinds of grains and grain products. These products will include such materials as wheat, corn, barley, or rice. In stored food products, they may be found in materials like macaroni or spaghetti. Adult weevils will feed on the same foods as the larvae. However, because they do not need to develop in the inside of whole grains like larvae do, they are not limited to just one grain or in other words, they are not restricted in their diets.
  • feeding deterrence of crops by agricultural pests such as hemiptera, lepidoptera and coleoptera is obtained by contact of the insects with at least one of the compounds of the structure (I)
  • R 1 is selected from H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
  • R 2 is selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
  • R 3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, -(CH 2 ) n OH, -C(O)OR 5 , -CH 2 C(O)OR 7 , - CH 2 C(O) R 8 , -C(O)NR 9 R 10 , and -CH 2 C(O)NR 11 R 12 where each of R 5 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms and n is an integer of from 1 to 12; the bond between the 2 and 3 positions in the ring structure may be a single or a double bond; and wherein the compounds of structure (I) contain from 9 to 20 total carbon atoms in the compounds.
  • the invention also includes optical isomers, diaste
  • the feeding deterrence compounds of this invention which could be applied directly to crops, seeds, agricultural or ornamental trees, plants, vegetation, produce or packaging materials for crops, have low mammalian toxicity and are similar to naturally occurring materials used in flavor/fragrance applications. Therefore, these provide a better method of control for farmers and home owners. Additionally, the feeding deterrence compounds of this invention have the potential to be used on organic crops.
  • the compounds of structure (I) may be employed to defer feeding by agricultural pests such as hemiptera, lepidoptera and coleoptera which include, but are not limited to, stink bugs, codling moth larvae and granary weevils.
  • the active compounds of structure (I) may be employed in any suitable formulation, such as, but not limited to, direct spray formulations, fogger formulations, microencapsulated formulations, soil treatment formulations, seed treatment formulations, injectable formulations for injection into the plant and formulations for use in evaporative devices.
  • R 2 is selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
  • R 3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms -(CH 2 ) complicatOH, -C(O)OR 5 , -CH 2 C(O)OR 7 , - CH 2 C(O)R8, -C(O)NR 9 R 10 , and -CH 2 C(O)NR 11 R 12 where each of R 5 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is n integer of from 1 to 12; the bond between the 2 and 3 positions in the ring structure may be a single or a double bond; and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms in the compounds.
  • the invention also includes optical isomers, diastereomers and
  • a preferred group of feeding deterrence compounds are those compounds of Structure (I) wherein;
  • Another preferred group of feeding deterrence compounds are those compounds of structure (I) wherein;
  • Another preferred group of feeding deterrence compounds are those compounds of structure (I) wherein
  • R 0, X is O, y is 1 or 2, each Z is selected from (CH) and (CH 2) , the bond between positions 2 and 3 of the rings is a single or double bond, more preferably a single bond, one of R 1 and R 2 is H and the other of R 1 and R 2 is a branched or straight chain, saturated or unsaturated hydrocarbyl group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R 3 is selected from -C(O)OR 5 and -CH 2 C(O)R 8 where R 5 and R 7 are each selected from a hydrocarbyl group containing from 1 to 6 carbon atoms, and more preferably 3 to 5 carbon atoms and still more preferably-CH 3 and wherein the total number of carbon atoms in the compounds of structure (I) is from 9 to 20, more preferably from 9 to 14 total carbon atoms.
  • Another preferred group of feeding deterrence compounds are those compounds of structure (I) wherein
  • R 0, X is O, y is 1 or 2, each Z is selected from (CH) and (CH 2) , the bond between positions 2 and 3 in the ring is a single bond, R 1 is a branched or straight chain, saturated or unsaturated alkyl group containing from 5 to 13 carbon atoms, R 2 is H or-CH 3 , R 3 is H, and more preferably where R ! is an alkyl group of from 5 to 10 carbon atoms such that the compound of structure (I) contains from 11 to 14 total carbon atoms.
  • the active compounds of structure (I) may be employed in any suitable formulation, such as, but not limited to, direct spray formulations, fogger formulations, microencapsulated formulations, soil treatment formulations, seed treatment formulations, injectable formulation for injection into the plant and formulations for use in evaporative devices.
  • the formulations of the active compounds will be such that the food or crops being treated will have from about 0.0S to about 250 mg/sq. in., preferably about 0.25 to about 50 mg/sq. in., of the active compounds thereon.
  • Preferred compounds of structure (I) include methyl apritone, methyl dihydrojasmonate, propyl dihydrojasmonate, gamma-dodecalactone, gamma-tridecalactone, gamma methyl dodecalactone, gamma methyl tridecalactone, 3-methyl-5-propyl-2-cyclohexenone, 3-methyl-5-isobutyl-2-cyclohexenone, 3- methyl-5-isobutyl-2-cyclohexenol, 3-methyl-5-pentyl-2-cyclohexenone and 3-methyl-5-heptyl-2- cyclohexenone.
  • a test was designed to measure the repellency as feeding deterrence in brown marmorated stink bugs (BMSB).
  • BMSB brown marmorated stink bugs
  • Five replicates of S BMSBs were introduced into test arenas, containing one 60mm x 15mm Petri dish with treated filter papers in which a food source (green bean) was attached, at the start of the test.
  • the small Petri dishes containing the treated filter paper and food source were covered with a fitted Petri dish lid in between observation times, and were removed 5 minutes before each observation time to prevent stink bugs from feeding until sated.
  • the distribution of the BMSBs was observed and documented hourly for S hours.
  • Another test was designed to measure the repellency as feeding deterrence in Codling Moth larvae.
  • the treatment was applied to the surface of a proprietary laboratory media in a tray with wells for each compound. The media was allowed to dry for 30-60 minutes so that larvae were not exposed to it as a liquid.
  • One first instar codling moth larva was then placed on the treated media.
  • the cover film was placed on the tray to prevent escapes.
  • Ten additional replicates treated with a 57% ethanol solution were prepared to serve as controls. The larvae were observed at 24 hours to determine if they burrowed into the media. After the 24 hour reading, the larvae were extracted from the media to record any mortality.
  • the feeding deterrent compounds of this invention may be blended with active repellents or toxicants including, but not limited to, NN-Diethyl- w-toluamide (DEET®) and p-Menthane-3,8-diol (PMD).
  • active repellents or toxicants including, but not limited to, NN-Diethyl- w-toluamide (DEET®) and p-Menthane-3,8-diol (PMD).

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Insects & Arthropods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catching Or Destruction (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

FEEDING DETERRENCE IN AGRICULTURAL PESTS SUCH AS HEMIPTERA,
LEPIDOPTERA AND COLEOPTERA
Field of the Invention
[0001] This invention relates to the use of compounds as agents that deter feeding of crops by agricultural pests such as hemiptera, lepidoptera and coleoptera including, but not limited to, stink bugs, codling moth larvae and granary weevils.
[0002] The active feeding deterrence agents of this invention are an effective control agent against agricultural pests such as hemiptera, lepidoptera and coleoptera. Hemiptera includes cicadas, aphids and stink bugs such as the Brown Marmorated Stink Bug. Lepidoptera includes butterflies and moths such as the Codling Moth. Coleoptera are beetles and the order contains granary weevils.
Background to the Invention
[0003] Agricultural pests including but not limited to the brown marmorated stink bug, codling moth and granary weevil are known to feed on various crops causing damage to fruits, vegetables and other plant life. The cost of this damage is extensive and leads to hardship among growers.
[0004] In the Mid-Atlantic region, where brown marmorated stink bugs are well established, they caused an estimated $37 million in damage in apple crops alone in 2010, the most recent year for which data are available. [Darryl Fears, "Stink bugs migrating to deep south", Washington Post, March 16, 2012]. Aside from apples, the bug will feed on nearly anything, including cherries, tomatoes, grapes, lima beans, soybeans, green peppers and peaches.
[0005] Codling moth larvae penetrate into apples and pears and tunnel to the core, leaving holes in the fruit that are filled with reddish-brown, crumbly droppings. If left uncontrolled, larvae can cause substantial damage, often infesting 20 to 90% of the fruit, depending on the variety and location. Late maturing varieties are more likely to suffer severe damage than early varieties. [J. L. Caprile and P.M. Vossen, Pest Notes: Codling Moth UC ANR Publication 7412, May 2011].
[0006] In walnuts, codling moth larvae feed on the kernels. Nuts damaged early in the season when the nuts are quite small will drop off trees soon after damage occurs. Nuts damaged later in the season will remain on trees, but their kernels are inedible. Walnuts aren't as favored a host as apples and pears, and untreated trees might incur very little to modest damage (10 to 15% of the nuts), depending on the variety and location. [Pest Notes, May 2011]
[0007] Phosmet, a phthalimide-derived, non-systemic, organophosphate insecticide is the primary means of controlling codling moth damage to apples. This material is on the US Emergency Planning list of extremely hazardous substances and is highly toxic to bees. The materials covered in this patent application would be a much gentler means of deterring the larvae and controlling moth infestation.
[0008] Granary weevils are attracted to and will attack all kinds of grains and grain products. These products will include such materials as wheat, corn, barley, or rice. In stored food products, they may be found in materials like macaroni or spaghetti. Adult weevils will feed on the same foods as the larvae. However, because they do not need to develop in the inside of whole grains like larvae do, they are not limited to just one grain or in other words, they are not restricted in their diets.
[http://www.pestmall.com/blog/pest-info/other-pests/granary-weevil-biology]
[0009] Control of weevils is quite difficult as they live and breed in our food sources. Use of pyrethrins is an option, but food shouldn't be sprayed directly. Use of our materials may be sprayed directly on crops, seeds, agricultural or ornamental trees, plants, vegetation, produce or packaging materials so they provide a better alternative to traditional insecticides.
Summary of the Invention
[0010] In accordance with this invention, feeding deterrence of crops by agricultural pests such as hemiptera, lepidoptera and coleoptera is obtained by contact of the insects with at least one of the compounds of the structure (I)
Figure imgf000004_0001
wherein:
R is selected from -OH, =O, -OC(O)R4, -OR6, and -(OR6)2, wherein each R6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R4 is a branched or straight chain, saturated or unsaturated, hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH2 with the proviso that when X is O R can only be =0; each Z is independently selected from (CH) and (CH2); y is a numeral selected from 1 and 2;
R1 is selected from H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
R2 is selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
R3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, -(CH2)nOH, -C(O)OR5, -CH2C(O)OR7, - CH2C(O) R8, -C(O)NR9R10, and -CH2C(O)NR11R12 where each of R5, R7, R8, R9, R10 , R11 and R12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms and n is an integer of from 1 to 12; the bond between the 2 and 3 positions in the ring structure may be a single or a double bond; and wherein the compounds of structure (I) contain from 9 to 20 total carbon atoms in the compounds. The invention also includes optical isomers, diastereomers and enantiomers of the compounds of structure (I). Thus, at all stereocenters where stereochemistry is not explicitly defined, all possible epimers are envisioned.
[001 1] The feeding deterrence compounds of this invention, which could be applied directly to crops, seeds, agricultural or ornamental trees, plants, vegetation, produce or packaging materials for crops, have low mammalian toxicity and are similar to naturally occurring materials used in flavor/fragrance applications. Therefore, these provide a better method of control for farmers and home owners. Additionally, the feeding deterrence compounds of this invention have the potential to be used on organic crops.
[0012] The compounds of structure (I) may be employed to defer feeding by agricultural pests such as hemiptera, lepidoptera and coleoptera which include, but are not limited to, stink bugs, codling moth larvae and granary weevils. The active compounds of structure (I) may be employed in any suitable formulation, such as, but not limited to, direct spray formulations, fogger formulations, microencapsulated formulations, soil treatment formulations, seed treatment formulations, injectable formulations for injection into the plant and formulations for use in evaporative devices.
Detailed Description of the Invention
[0013] Deterrence of feeding by agricultural pests such as hemiptera, lepidoptera and coleoptera including, but not limited to, stink bugs, codling moth larvae and granary weevils is obtained by contact of the insects with at least one of the compounds of the structure (I)
Figure imgf000006_0001
wherein
R is selected from -OH, =O, -OC(O)R4, -OR6, and -(OR6)2, wherein each Re is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R4 is a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH2 with the proviso that when X is O R can only be =0; each Z is independently selected from (CH) and (CH2); y is a numeral selected from 1 and 2; R1 is selected from H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
R2 is selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
R3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms -(CH2)„OH, -C(O)OR5, -CH2C(O)OR7, - CH2C(O)R8, -C(O)NR9R10, and -CH2C(O)NR11R12 where each of R5, R7, R8, R9, R10, R11 and R12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is n integer of from 1 to 12; the bond between the 2 and 3 positions in the ring structure may be a single or a double bond; and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms in the compounds. The invention also includes optical isomers, diastereomers and enantiomers of the named structures. Thus, at all stereocenters where stereochemistry is not explicitly defined, all possible epimers are envisioned.
[0014] A preferred group of feeding deterrence compounds are those compounds of Structure (I) wherein;
R is selected from -OH and =0, X is CH2, y is 1 or 2, each Z is selected from (CH) and (CH2), the bond between positions 2 and 3 in the ring is a single bond, one of R1 and R2 is H or -CH3 and the other of R1 and R2 is a branched or straight chain, saturated or unsaturated hydrocarbyl group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R3 is H.
[0015] Another preferred group of feeding deterrence compounds are those compounds of structure (I) wherein;
R is selected from -OH and =0, more preferably =0, X is CH2, y is 1 or 2, more preferably 1, each Z is selected from (CH) and (CH2), the bond between positions 2 and 3 in the ring is a single or double bond, more preferably a single bond, one of R1 and R2 is H and the other of R1 and R2 is a branched or straight chain, saturated or unsaturated hydrocarbyl group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R3 is selected from -C(O)OR5 and -CH2C(O)R8 where R5 and R8 are each selected from a straight chain or branched, saturated or unsaturated hydrocarbyl group containing from 1 to 6 carbon atoms, and more preferably 3 to 5 carbon atoms and still more preferably -CH3.
[0016] Another preferred group of feeding deterrence compounds are those compounds of structure (I) wherein
R is =0, X is O, y is 1 or 2, each Z is selected from (CH) and (CH2), the bond between positions 2 and 3 of the rings is a single or double bond, more preferably a single bond, one of R1 and R2 is H and the other of R1 and R2 is a branched or straight chain, saturated or unsaturated hydrocarbyl group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R3 is selected from -C(O)OR5 and -CH2C(O)R8 where R5 and R7 are each selected from a hydrocarbyl group containing from 1 to 6 carbon atoms, and more preferably 3 to 5 carbon atoms and still more preferably-CH3 and wherein the total number of carbon atoms in the compounds of structure (I) is from 9 to 20, more preferably from 9 to 14 total carbon atoms.
[0017] Another preferred group of feeding deterrence compounds are those compounds of structure (I) wherein
R is =0, X is O, y is 1 or 2, each Z is selected from (CH) and (CH2), the bond between positions 2 and 3 in the ring is a single bond, R1 is a branched or straight chain, saturated or unsaturated alkyl group containing from 5 to 13 carbon atoms, R2 is H or-CH3, R3 is H, and more preferably where R! is an alkyl group of from 5 to 10 carbon atoms such that the compound of structure (I) contains from 11 to 14 total carbon atoms.
[0018] The active compounds of structure (I) may be employed in any suitable formulation, such as, but not limited to, direct spray formulations, fogger formulations, microencapsulated formulations, soil treatment formulations, seed treatment formulations, injectable formulation for injection into the plant and formulations for use in evaporative devices. The formulations of the active compounds will be such that the food or crops being treated will have from about 0.0S to about 250 mg/sq. in., preferably about 0.25 to about 50 mg/sq. in., of the active compounds thereon.
[0019] Representative examples of compounds of structure (I) include, but are not limited to,
Figure imgf000009_0002
Figure imgf000009_0001
Figure imgf000010_0001
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000013_0001
e
Figure imgf000014_0001
y py y
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000017_0003
Figure imgf000017_0001
Figure imgf000017_0002
[0020] Preferred compounds of structure (I) include methyl apritone, methyl dihydrojasmonate, propyl dihydrojasmonate, gamma-dodecalactone, gamma-tridecalactone, gamma methyl dodecalactone, gamma methyl tridecalactone, 3-methyl-5-propyl-2-cyclohexenone, 3-methyl-5-isobutyl-2-cyclohexenone, 3- methyl-5-isobutyl-2-cyclohexenol, 3-methyl-5-pentyl-2-cyclohexenone and 3-methyl-5-heptyl-2- cyclohexenone.
[0021] A test was designed to measure the repellency as feeding deterrence in brown marmorated stink bugs (BMSB). Five replicates of S BMSBs were introduced into test arenas, containing one 60mm x 15mm Petri dish with treated filter papers in which a food source (green bean) was attached, at the start of the test. The small Petri dishes containing the treated filter paper and food source were covered with a fitted Petri dish lid in between observation times, and were removed 5 minutes before each observation time to prevent stink bugs from feeding until sated. The distribution of the BMSBs was observed and documented hourly for S hours.
Figure imgf000018_0001
[0022] Another test was designed to measure the repellency as feeding deterrence in Codling Moth larvae. The treatment was applied to the surface of a proprietary laboratory media in a tray with wells for each compound. The media was allowed to dry for 30-60 minutes so that larvae were not exposed to it as a liquid. One first instar codling moth larva was then placed on the treated media. The cover film was placed on the tray to prevent escapes. Ten additional replicates treated with a 57% ethanol solution were prepared to serve as controls. The larvae were observed at 24 hours to determine if they burrowed into the media. After the 24 hour reading, the larvae were extracted from the media to record any mortality.
Figure imgf000018_0002
Figure imgf000019_0003
[0023] Mortality observations were also made for the above protocol. The control was the 57% ethanol:43% water solution.
Figure imgf000019_0001
[0024] Ten replicates of 30 kernels of wheat were immersed into the test compound and allowed to dry for 24 hours. The grains were then transferred to a test container, and 10 granary weevils were released. Test containers were secured and left for a 3 week period. At the end of this time, the wheat grains were examined for developing larvae and damage by larvae. The number of grains that contained developing larvae or that showed damage was recorded. Ten additional replicates treated with isopropyl alcohol were prepared to serve as controls.
Figure imgf000019_0002
Figure imgf000020_0001
[0025] The feeding deterrent compounds of this invention may be blended with active repellents or toxicants including, but not limited to, NN-Diethyl- w-toluamide (DEET®) and p-Menthane-3,8-diol (PMD).
[0026] While the invention has been described herein with reference to the specific embodiments thereof, it will be appreciated that changes, modification and variations can be made without departing from the spirit and scope of the inventive concept disclosed herein. Accordingly, it is intended to embrace all such changes, modification and variations that fall with the spirit and scope of the appended claims.

Claims

I claim
1. A method for deterring the feeding of one or more agricultural pests such as hemiptera, lepidoptera and coleoptera on food or crops is obtained by contact of the insects with at least one of the compounds of the structure (I)
Figure imgf000021_0001
wherein
R is selected from the group consisting of -OH, =0, -OC(O)R4, -OR6, and -(OR6)2, wherein each R6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R4 is a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH2 with the proviso that when X is O R can only be =0; each Z is independently selected from the group consisting of (CH) and (CH2); y is a numeral selected from 1 and 2;
R1 is selected from the group consisting of H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
R2 is selected from the group consisting of H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
R3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, -(CH2)nOH, -C(O)OR5, -CH2C(O)OR7, - CH2C(O)R8, -C(O)NR9R10, and -CH2C(O)NR11R12 where each of R5, R7, R8, R9, R10, R11 and R12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is n integer of from 1 to 12; the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (I) contain from 9 to 20 total carbon atoms in the compounds.
2. The method according to claim 1 wherein the agricultural pest is selected from the group consisting of stink bugs, codling moth larvae and granary weevils.
3. The method according to claim 1 wherein the compounds of structure (1) have from 10 to 16 carbon atoms in the compound.
4. The method according to claim 1 wherein the at least one compound of structure (I) is a compounds wherein:
R is selected from the group consisting of -OH and =0, X is CH2, y is 1 or 2, each Z is selected from the group consisting of (CH) and (CH2), the bond between positions 2 and 3 in the ring is a single bond, one of R1 and R2 is H or -CH3 and the other of R1 and R2 is a hydrocarbyl group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R3 is H.
5. The method of claim 1 wherein the at least one compound of structure (I) is a compound wherein: R is selected from the group consisting of -OH and =0, X is CH2, y is 1 or 2, each Z is selected from (CH) and (CH2), the bond between positions 2 and 3 in the ring is a single or double bond, one of R1 and R2 is H and the other of R1 and R2 is a hydrocarbyl group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R3 is selected from the group consisting of -C(O)OR5 and -CH2C(O)R8 where R5 and R8 are each selected from a hydrocarbyl group containing from 1 to 6 carbon atoms.
6. The method according to claim S wherein R is =0, y is 1, the bond between positions 2 and 3 in the ring is a single bond, and R2 and R5 are each -CH3.
7. The method according to claim 1 wherein the at least one compound of structure (I) is a compounds wherein:
R is =0, X is O, y is 1 or 2, each Z is selected from the group consisting of (CH) and (CH2), the bond between positions 2 and 3 of the rings is a single or double bond, one of R1 and R2 is H and the other of R1 and R2 is a hydrocarbyl group containing group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R3 is selected from the group consisting of -C(O)OR5 and -CH2C(O)R8 where R5 and R8 are each selected from a hydrocarbyl group containing from 1 to 6 carbon atoms and wherein the total number of carbon atoms in the compounds of structure (I) is from 11 to 17.
8. The method according to claim 7 wherein the bond between positions 2 and 3 of the rings is a single bond and R5 and R7 are each selected from a hydrocarbyl group containing from 3 to 5 carbon atoms.
9. The method according to claim 7 wherein the bond between positions 2 and 3 of the rings is a single bond and R5 and R7 are each -CH3.
10. The method according to claim 1 wherein at least one compound of structure (I) is a compound wherein:
R is =0, X is O, y is 1 or 2, each Z is selected from (CH) and (CH2), the bond between positions 2 and 3 in the ring is a single bond, R1 is an alkyl group containing from 5 to 13 carbon atoms, R2 is selected from the group consisting of H or -CH3, R3 is H.
11. The method according to claim 10 wherein:
R1 is an alkyl group of from 5 to 10 carbon atoms such that the compound of structure (I) contains from 11 to 14 total carbon atoms.
12. The method according to claim 1 wherein the compound of structure (I) is selected from the group consisting of :
Figure imgf000024_0001
Figure imgf000025_0001
13. The method according to claim 1 wherein the compound of structure (I) is selected from the group consisting of:
Figure imgf000026_0001
Figure imgf000026_0002
Figure imgf000027_0001
Figure imgf000027_0002
Figure imgf000028_0003
and
Figure imgf000028_0001
14. The method according to claim 1 wherein the compound of structure (I) is selected from the group consisting of
Figure imgf000028_0002
Figure imgf000029_0001
15. The method according to claim 1 wherein the compound of structure (I) is selected from the group consisting of:
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
16. The method according to claim 1 wherein the compound of structure (I) is selected from the group consisting of
-
Figure imgf000032_0002
Figure imgf000033_0001
17. The method according to claim 1 wherein the at least one compound of structure (I) is applied to crops, agricultural or ornamental trees, plants, vegetation, produce or packaging materials for plants or crops by way of a formulation selected from the group consisting of direct spray formulations, fogger formulations, microencapsulated formulations, soil treatment formulations, seed treatment formulations, injectable formulations for injection into or onto plants or crops, and formulations for evaporative devices.
18. The method of claim 1 wherein the compound of structure (I) is selected from the group consisting of :
methyl apritone, methyl dihydrojasmonate, propyl dihydrojasmonate, gamma-dodecalactone, gamma- tridecalactone, gamma methyl dodecalactone, gamma methyl tridecalactone, 3-methyl-5-propyl-2- cyclohexenone, 3-methyI-5-isobutyl-2-cyclohexenone, 3-methyl-5-isobutyl -2-cyclohexenol, 3-methyl-5- pentyl-2-cyclohexenone and 3-methyI-5-heptyl-2-cyclohexenone.
PCT/US2013/000120 2012-05-02 2013-04-30 Feeding deterrence in agricultural pests such as hemiptera, lepidoptera and coleoptera Ceased WO2013165476A1 (en)

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US14/390,826 US10111429B2 (en) 2012-05-02 2013-04-30 Feeding deterrence in agricultural pests such as hemiptera, lepidoptera and coleoptera
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EP13784833.9A EP2925126A4 (en) 2012-05-02 2013-04-30 INDUCTION OF ANTIAPPETENCE IN AGRICULTURAL PARASITES SUCH AS HEMIPTERES, LEOPARDOPTERS AND COOPERATORS
US16/131,412 US20190082690A1 (en) 2012-05-02 2018-09-14 Feeding deterrence in agricultural pests such as hemiptera, lepidoptera and coleoptera
US16/531,446 US11224223B2 (en) 2012-05-02 2019-08-05 Feeding deterrence of pests such as Hemiptera, Lepidoptera and Coleoptera

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